Trifluoroacetic acid methylene chloride → 2-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)ethylcarbamate TFA salt

HRID 218443Notes

Reaction equation

HRID 218443 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([O:22][CH2:23][CH2:24][NH:25][C:26]([O:28]C)=[O:27])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:5]=[CH:6][CH:7]=1.C(Cl)Cl.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>>[OH:39][C:33]([C:35]([F:38])([F:37])[F:36])=[O:34].[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[O:22][CH2:23][CH2:24][NH:25][C:26](=[O:27])[OH:28])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 595984981-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)[2-[(methoxycarbonyl)amino]ethoxy]methyl]-, 1,1-dimethylethyl ester, (3R)-

Product 1

HCID 1317297722-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)ethylcarbamate TFA salt

Procedure

The solution of (R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-(methoxycarbonylamino)ethoxy)methyl)piperidine-1-carboxylate (2.247 g, 5.26 mmol) in mixed solvent of DCM/TFA (24 mL, 3:1, v/v) was stirred at rt for 30 min. The solvents was removed in vacuo to produce 2-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)ethylcarbamate TFA salt in quantitative yield. MS ESI+ve m/z 327 (M+H).

Workup

  1. customThe solvents was removed in vacuo

Sources & evidence

ORD record
ord-9bae557d4d244f8ea6a4d40cb00abee4
Source dataset
uspto-grants-2012_06
Patent number
US08198453B2

Reaction notes

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